JP2005512309A6 - Spin-on antireflection coating for photolithography - Google Patents

Abstract

  The antireflective coating material for ultraviolet photolithography includes at least one absorbing compound and at least one pH adjuster that are introduced into the spin-on material. Suitable absorbing compounds are those that absorb around wavelengths such as 365 nm, 248 nm, 193 nm, and 157 nm that can be used for photolithography. Suitable pH modifiers not only adjust the pH of the final spin-on composition, but also the chemical performance and characteristics of the final spin-on composition that becomes part of the layered material, electronic component, or semiconductor component, machine Affect the physical performance as well as the structural configuration, making the final spin-on composition more compatible with the resist material being combined. More specifically, the pH adjusting agent strongly influences the polymer characteristics, the structural configuration, and the spatial directionality, and improves the surface characteristics of the antireflection film so as to obtain optimum resist performance. That is, a pH adjusting agent that merely adjusts the pH of the spin-on material and does not affect the mechanical properties and structural configuration of the spin-on composition or the combined resist material is not considered herein. A method of making an absorbable and pH adjusted spin-on material includes mixing at least one organic absorbing compound and at least one pH adjusting agent with at least one silane reactant during the synthesis of the spin-on material and composition. Included.

Description

The present invention relates generally to spin-on glass materials, and more particularly to a light-absorbing spin-on glass material for use as an antireflective layer in photolithography and a method for producing the material.

BACKGROUND OF THE INVENTION In order to meet the demand for faster operation than the background of the invention, the characteristic dimensions of the feature space of integrated circuit devices continue to decrease. The manufacture of smaller sized devices creates new challenges in many processes conventionally used in semiconductor manufacturing. One of the most important in these manufacturing processes is photolithography.

  It has long been recognized that variations (variations) in the line width of a pattern produced by photolithography can be attributed to optical interference due to light reflected by an underlying layer of a semiconductor wafer. In addition, a variation (variation) in the thickness of the photoresist due to the topography of the under layer also causes a variation in the line width. An anti-reflective coating (ARC) applied under the photoresist layer has been used to prevent interference due to reflection of the irradiated light. In addition, the anti-reflective coating improves the line width variation across steps by partially planarizing the topography of the wafer and making the photoresist thickness more uniform.

  Organic polymer films (especially organic polymer films that absorb i-line (365 nm) and g-line (436 nm) wavelengths conventionally used to expose photoresists, and recently used 157 nm, 193 nm , An organic polymer film that absorbs a wavelength of 248 nm) has been used as an antireflective coating or has been tested as an antireflective coating. However, since organic ARC shares many chemical properties with organic photoresists, the process sequences that can be used are limited. In addition, ARC (which includes both organic and inorganic ARC) is mixed with the photoresist layer. Organic ARC and inorganic ARC may mix with the photoresist layer if not fully baked or cured.

  One way to avoid such mixing is to add a thermosetting binder as an additional component to the organic ARC, as described, for example, in US Pat. No. 5,693,691 (Flaim et al). As described in U.S. Pat. No. 4,910.122 (Arnold et al), the dye may optionally be organic ARC's, as well as additional additives (eg, wetting agents, adhesion promoters, preservatives, plasticizers, etc.). Can be introduced. Some of these mixed-up issues may be solved, but the lack of 86 ° -90 ° uniformity of resist edges due to the combined ARC layer has been It was not solved by the technology.

  Also, the photoresist and the antireflective film interact with each other, and when a pattern is developed in the resist, the resist may “fall over” due to the chemical nature of the antireflective film and / or resist material. That is, the patterned resist sidewall cannot maintain an angle of about 90 degrees with respect to the antireflective coating after the photoresist is developed. Instead, the resist is at 120 ° or 80 ° with respect to the antireflection film. Such drawbacks are also a manifestation of the unnecessarily chemical, physical or mechanical compatibility of the photoresist material and the anti-reflective coating.

Another group of materials that can be used as an antireflective layer is a spin-on glass (SOG) composition containing a dye. U.S. Pat. No. 4,587,138 by Yau et al. Describes mixing a dye (such as Basic Yellow # 11) in a spin-on glass in an amount of about 1% by weight. U.S. Pat. No. 5,100,503 to Allman et al. Describes inorganic dyes (e.g., TiO ₂ , Cr ₂ O ₇ , MoO _Four , MnO _Four Or SCO _Four ) And cross-linked polyorganosiloxanes containing adhesion promoters are described. Allman et al. Also teach that the spin-on glass composition acts as a planarizing layer. However, the combination of spin-on glass and dyes disclosed so far is not suitable for the exposure of deep ultraviolet light sources (especially 248 and 193 nm) used to produce small-sized devices. Furthermore, not all dyes can be easily introduced into all spin-on glass compositions. Also, even though these ARCs are chemically different from the organic ARCs described above, the combined resist layer is a chemical, physical and mechanical incompatibility between the ARC layer and the resist layer. Can be “collapsed” after development, due to common problems when combined with anti-blocking films.

  Therefore, a) absorbs strongly and uniformly in the ultraviolet region, b) does not `` break '' the resist material or protrude from the intended resist line, c) the photoresist developer and the above SOG antireflection film Absorptive spin-on glass antireflective coatings and lithographic materials that are insensitive to the manufacturing process are desired to advance the manufacturing of layered materials, electronic components, and semiconductor components.

SUMMARY OF THE INVENTION An antireflective coating material for ultraviolet photolithography comprises at least one absorptive organic compound and at least one pH adjuster that are introduced into an inorganic spin-on material or a spin-on glass (SOG) material.

This spin-on material is an inorganic-based compound (eg, a silicon-based compound, a gallium-based compound, an arsenic-based compound, a boron-based compound, or a combination of these inorganic elements and materials) Comprising. Some of the possible spin-on glass materials may include methyl siloxane, methyl silsesquioxane, phenyl siloxane, phenyl silsesquioxane, methyl phenyl siloxane, methyl phenyl silsesquioxane, silicate polymers, and mixtures thereof. . As used herein, a group known as “spin-on glass materials” includes siloxane polymers, hydrogen siloxane polymers of the general formula (H _0-1.0 SiO _1.5-2.0 ) _x and formula (HSiO _1.5 ) _x . Hydrogensilsesquioxane polymers having x where x is greater than about 4 may be included. A copolymer of hydrogensilsesquioxane and alkoxyhydridosiloxane or hydroxyhydridosiloxane may also be included. The spin-on glass material additionally comprises an organic hydridosiloxane polymer of the general formula (H _0-1.0 SiO _1.5-2.0 ) _n (R _0-1.0 SiO _1.5-2.0 ) _m and a general formula (HSiO _1.5 ) _n (RSiO _1.5 ) _m organic hydridosilsesquioxane polymers, where m is greater than 0, n and m are synthesized greater than about 4, and R is alkyl or aryl.

  Absorbing compounds suitable for introduction into this spin-on-glass material have strong absorbance at wavelengths below 375 nm, or below about 260 nm. Specifically, suitable light-absorbing compounds have absorption at wavelengths around 248 nm, 193 mn, 157 nm, or other ultraviolet wavelengths (eg 365 nm) that can be used in photolithography. . The chromophores of suitable compounds typically have at least one benzene ring, and if they have more than one benzene ring, these rings may be fused, even if they are fused. It does not have to be. Absorbable compounds that can be introduced have accessible reactive groups linked to a chromophore, which are hydroxyl groups, amine groups, carboxylic acid groups, and 1, 2 Or a silyl group substituted with a silicon or halogen atom substituent bonded to three alkoxy groups. The reactive group may be directly bonded to the chromophore, or may be bonded to the chromophore through a hydrocarbon bridge or an oxygen bond. The chromophore may also contain silicon-based compounds or polymers similar to those used to make spin-on glass materials.

  A pH adjuster is added to the mixture of spin-on materials and a portion of the absorbing organic compound to control the pH of the final spin-on composition with the resist layer and other combined layers with which the final spin-on composition is combined. A compound, material, or solution that “adjusts” or adjusts to a pH such that it is compatible. However, the pH adjuster not only adjusts the pH of the final spin-on composition, but also the chemical performance, mechanical properties of the final spin-on composition, such as a layered material, electrical component, or part of a semiconductor component. It is preferable to affect performance and structural configuration, and to better match the resist material combined with the spin-on composition. More specifically, the pH adjuster strongly acts on the polymer properties, structural configuration, and spatial orientation, and improves the surface characteristics of the antireflection film so that optimum resist performance can be obtained. That is, pH adjusters that simply adjust the pH of the spin-on material and do not affect the mechanical properties and structural configuration of the spin-on composition and the resist material being combined are not contemplated herein.

  Another aspect of the invention provides a method for synthesizing an absorptive spin-on composition. Spin-on materials are typically silane and silicon-based reactants (eg, triethoxysilane, tetraethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane, tetramethoxysilane, methyltrimethoxysilane, trimethoxysilane, dimethyldimethoxy). Silane, phenyltriethoxysilane, phenyltrimethoxysilane, diphenyldiethoxysilane, and diphenyldimethoxysilane). However, gallium, arsenic, germanium, boron, and similar elements and materials can also be used in combination with or alone with silicon atoms to produce spin-on materials. Halosilanes (particularly chlorosilanes) can also be used as silane reactants.

  A method for producing an absorptive spin-on composition comprises at least one inorganic-based composition, at least one absorbable organic compound, at least one pH adjuster, an acid / water mixture (eg nitric acid / Water mixture), and mixing at least one solvent to form a reaction mixture; refluxing the reaction mixture to produce an absorbing spin-on composition. The resulting spin-on composition is then diluted with at least one solvent to produce a coating solution for producing films of various thicknesses. Moreover, a pH adjuster can also be added during a reflux process or after a reflux process.

  In another method of manufacturing an absorbent spin-on composition, at least one inorganic-based composition, at least one absorbable organic compound, at least one pH adjuster, and at least one solvent are mixed. Thus, a reaction mixture can be produced. The reaction mixture is then refluxed to produce an absorptive spin-on composition. The resulting spin-on composition is diluted with at least one solvent to prepare a coating solution for producing films of various thicknesses. In this method, the pH adjusting agent is a conventional various acid / water mixture (a different acid may be added, a small amount of acid may be added, or a larger amount of water may be added). You can. However, regardless of the pH adjuster selected, the pH adjuster not only affects the pH, but also the chemical, mechanical, and physical properties of the ARC, and the combination of resist and ARC. The basic principle of better compatibility remains the same.

  In yet another aspect of the present invention, an absorptive spin-on composition includes at least one silicon-based compound, at least one absorptive organic compound that can be introduced (this is light having a wavelength of less than about 375 nm). And a pH adjuster. Further provided is an absorptive spin-on composition in which at least one silicon-based compound or absorbable organic compound that can be introduced comprises at least one alkyl group, alkoxy group, ketone group, or azo group. .

  Yet another aspect of the present invention provides a spin-on composition comprising an absorptive compound from the group of compounds comprising 9-anthracenecarboxy-alkyltrialkoxysilane. A method of synthesizing any of the 9-anthracenecarboxy-alkyltrialkoxysilanes includes mixing 9-anthracenecarboxylic acid, chloroalkyltrialkoxysilane, triethylamine, and a solvent to form a reaction mixture; Reflux; cooling the refluxed reaction mixture to form a precipitate and a remaining solution; further, filtering the remaining solution to produce a liquid 9-anthracenecarboxy-alkyltrialkoxysilane. It is.

DETAILED DESCRIPTION An anti-reflective coating material for ultraviolet photolithography includes at least one absorbing organic compound and at least one pH adjuster that can be introduced into an inorganic spin-on material or a spin-on glass (SOG) material. The absorbent spin-on composition is dissolved in a suitable solvent to form a coating solution and applied to layers of various materials in the manufacture of layered materials, electronic devices, and semiconductor devices. Absorptive spin-on antireflective coatings are designed to be easily incorporated into current layered materials, electronic components, or semiconductor manufacturing processes. Some of the properties that facilitate this incorporation are a) durability to the developer, b) thermal stability in standard photoresist processes, and c) selective removal to the underlayer.

Spin-on materials Possible spin-on materials include inorganic-based compounds (eg, silicon-based compounds, gallium-based compounds, germanium-based compounds, arsenic-based compounds, boron-based compounds, or combinations thereof) is there. As used herein, the terms “spin-on material”, “organic spin-on material”, “spin-on composition”, and “inorganic spin-on composition” may be interchangeable and Or a solution or composition thereof that can be spun on the surface. Also, the term “spin-on glass material” refers to a portion of “inorganic spin-on material”, and the spin-on glass material is considered to indicate a spin-on material that includes silicon-based compounds and / or polymers in whole or in part. Silicon-based compounds include, for example, siloxane compounds (eg, methyl siloxane, methyl silsesquioxane, phenyl siloxane, phenyl silsesquioxane, methyl phenyl siloxane, methyl phenyl silsesquioxane, silazane polymers, silicate polymers, and And a mixture thereof). A possible silazane polymer is perhydrosilazane, which has a “transparent” polymer backbone to which chromophores can be attached.

As used herein, the term “spin-on-glass material” also refers to siloxane polymers and block polymers, hydrogen siloxane polymers of the general formula (H _0-1.0 SiO _1.5-2.0 ) _x , and formula (HSiO _1.5 ) a hydrogensilsesquioxane polymer having _x (where x is greater than about 4). Also included are copolymers of hydrogensilsesquioxane and alkoxyhydridosiloxane or hydroxyhydridosiloxane. The spin-on glass material additionally comprises an organic hydridosiloxane polymer of the general formula (H _0-1.0 SiO _1.5-2.0 ) _n (R _0-1.0 SiO _1.5-2.0 ) _m and a general formula (HSiO _1.5 ) _n (RSiO _1.5 ) _m organic hydridosilsesquioxane polymers, wherein m is greater than 0, the sum of n and m is greater than about 4, and R is alkyl or aryl. Some useful organohydridosiloxane polymers, R is an aryl group an alkyl group or a C ₆ -C ₁₂ of C ₁ -C _20, sum of n and m is from about 4 to about 5000. This organohydridosiloxane and organohydridosilsesquioxane polymer are spin-on polymers that are shown to each other. Among the specific examples are alkyl hydridosiloxanes (eg, methyl hydride siloxane, ethyl hydride siloxane, propyl hydrido siloxane, t-butyl hydrido siloxane, phenyl hydrido siloxane); and alkyl hydridosilsesquioxanes (eg, methyl hydridosyl). Sesquioxane, ethyl hydrido silsesquioxane, propyl hydrido silsesquioxane, t-butyl hydrido silsesquioxane, phenyl hydrido silsesquioxane), and combinations thereof.

Absorbing compounds Many naphthalene-based compounds, phenanthrene-based compounds, and anthracene-based compounds have strong absorption at 248 nm and below. Benzene-based compounds (here, the same meaning as phenyl-based compounds) have strong absorption at wavelengths shorter than 200 nm. These naphthalene-based compounds, anthracene-based compounds, phenanthrene-based compounds, and phenyl-based compounds are often referred to as dyes, but the absorption of these compounds is not limited to only wavelengths in the visible range. Therefore, in this specification, the term absorptive compound is used. However, not all of these absorptive compounds can be introduced into the spin-on material for use as an antireflective coating material. Absorptive compounds suitable for use in the present invention have definable absorption peaks at wavelengths such as 248 nm, 193 nm, 157 nm, or other ultraviolet wavelengths (eg 365 nm) that may be used in photolithography. ) Preferred “definable absorption peaks” are those whose width is at least 1 nm (where the width is measured by techniques generally known in the field of photolithography). In a further preferred embodiment, the definable absorption peak has a width of at least 5 nm. In an even more preferred embodiment, the definable absorption peak has a width of at least 10 nm.

  Suitable absorbing compound chromophores typically have at least one benzene ring, and if there are two or more benzene rings, the benzene rings may or may not be condensed. Absorbable compounds that can be introduced have accessible reactive groups attached to the chromophore. This reactive group includes a hydroxyl group, an amine group, a carboxylic acid group, a substituted silyl group that is silicon-bonded to one, two, or three “leaving groups” (eg, an alkoxy group or a halogen element). . Ethoxy groups or methoxy groups or chlorine atoms are often used as leaving groups. Preferred reactive groups include silicon alkoxy groups, silicon dialkoxy groups, and silicon trialkoxy groups (for example, silicon ethoxy groups, silicon diethoxy groups, silicon triethoxy groups, silicon methoxy groups, silicon dimethoxy groups, silicon trimethoxy groups). ) And halosilyl groups (for example, chlorosilyl, dichlorosilyl, and trichlorosilyl groups).

  Reactive groups may be linked directly to chromophores (eg, phenyltriethoxysilane), and oxygen bonds and hydrocarbon bridges (eg, 9-anthracenecarboxy-alkyltrialkoxysilane). It may be linked to the chromophore via Inclusion of silicon trialkoxy groups on the chromophore has been found to be advantageous, and in particular has been found to be advantageous for improving the stability of absorbent SOG films. Other useful absorptive compounds are those that have an azo group (-N = N-) and a reactive group that can be contacted and are linked to the benzene ring if absorption near 365 nm is desired in a specific application. The compounds having an azo group are particularly useful. The azo group may be included as part of a linear molecule, a cyclic molecule, or a hybrid molecule of a linear molecule and a cyclic molecule.

  The absorbing compound may be introduced interstitially into the substrate of the spin-on material. Further, the absorbing compound may be chemically bonded to the spin-on material or the polymer. In some possible embodiments, the absorbable compound that can be introduced forms a bond with the backbone of the spin-on material or the polymer backbone via a reactive group that can be contacted.

  Absorptive spin-on compositions and materials also include silicon-based compounds and absorbable organic compounds that can be introduced that absorb light at wavelengths below about 375 nm. Furthermore, in other embodiments, the at least one silicon-based compound or the absorbable organic compound that can be introduced will comprise at least one alkyl group, alkoxy group, ketone group, or azo group.

  Absorbable compounds suitable for use in the present invention include, for example, anthraflavic acid (1), 9-anthracenecarboxylic acid (2), 9-anthracenemethanol (3), 9-anthraceneethanol (4), 9- Anthracenepropanol (5), 9-anthracenebutanol (6), alizarin (7), quinizarin (8), primuline (9), 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone ( 10), 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenyl ketone (11), 2-hydroxy-4- (3-tributoxysilylpropoxy) -diphenyl ketone (12), 2-hydroxy-4 -(3-tripropoxysilylpropoxy) -diphenyl ketone (13), rosoleic acid (14), triethoxysilylpropyl-1,8-naphthalimide (15), trimethoxysilylpropyl-1,8-naphthalimide (16) , Tripropoxysil Propyl-1,8-naphthalimide (17), 9-anthracenecarboxy-methyltriethoxysilane (18), 9-anthracenecarboxy-ethyltriethoxysilane (19), 9-anthracenecarboxy-butyltriethoxysilane (20) 9-anthracenecarboxy-propyltriethoxysilane (21), 9-anthracenecarboxy-methyltrimethoxysilane (22), 9-anthracenecarboxy-ethyltributoxysilane (23), 9-anthracenecarboxy-methyltripropoxysilane ( 24), 9-anthracenecarboxy-propyltrimethoxysilane (25), phenyltriethoxysilane (26), phenyltrimethoxysilane (27), phenyltripropoxysilane (28), 10-phenanthrenecarboxy-methyltriethoxysilane ( 29), 10-phenanthrenecarboxy-ethyltriethoxysilane (30) 10-phenanthrenecarboxy-methyltrimethoxysilane (31), 10-phenanthrenecarboxy-propyltriethoxysilane (32), 4-phenylazophenol (33), 4-ethoxyphenylazobenzene-4-carboxy-methyltriethoxysilane ( 34), 4-methoxyphenylazobenzene-4-carboxy-ethyltriethoxysilane (35), 4-ethoxyphenylazobenzene-4-carboxy-propyltriethoxysilane (36), 4-butoxyphenylazobenzene-4-carboxy-propyl Triethoxysilane (37), 4-methoxyphenylazobenzene-4-carboxy-methyltriethoxysilane (38), 4-ethoxyphenylazobenzene-4-carboxy-methyltriethoxysilane (39), 4-methoxyphenylazobenzene-4 -Carboxy-ethyltriethoxysilane (40) 4-methoxyphenyl azobenzene-4-carboxy - propyltriethoxysilane (41), and combinations thereof. Chemical formulas of the absorbent compounds 1 to 41 are shown in FIGS. 1a to 1f. Favorable results include, for example, 9-anthracenecarboxy-methyltriethoxysilane (18), 9-anthracenemethanol (3), 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone (10) and rosole Obtained in combination with acid (14) and phenyltriethoxysilane (26). However, it should be noted that the above list of specific compounds is not an exhaustive list, and possible and preferred compounds may be selected from a group of chemical compounds including the above specific compounds. .

  Absorbable compounds 1-25 and 29-41 are commercially available from, for example, Aldrich Chemical Company (Milwaukee, Wis.). 9-anthracenecarboxy-alkyltrialkoxysilane is synthesized by an esterification method as described in the examples. Absorbable compounds 26-28 are commercially available from Gelest, Inc. (Tullytown, PA). Other phenyl-based absorbent compounds (of which many are commercially available from Gelest, Inc.) as absorbent compounds (26-28) include, for example, phenyl rings or substituted phenyl (eg, Examples include structures having silicon-based reactive groups into which (methylphenyl, chlorophenyl, and chloromethylphenyl) have been introduced. Specific examples of phenyl-based absorbent compounds include phenyltrimethoxysilane, benzyltrichlorosilane, chloromethylphenyltrimethoxysilane, and phenyltrifluorosilane, to name just a few. In addition, to name just a few, diphenylsilanes containing one or two “leaving groups” (eg, diphenylmethylethoxysilane, diphenyldiethoxysilane, and diphenyldichlorosilane) should also be introduced appropriately. Is a possible absorptive compound. Alkoxybenzoic acid including methoxybenzoic acid can also be used as an absorptive compound.

  A general method for synthesizing 9-anthracenecarboxy-alkyltrialkoxysilane compounds comprises using 9-anthracenecarboxylic acid and a chloromethyltrialkoxysilane compound as reactants. In particular, in the method for synthesizing 9-anthracenecarboxy-methyltriethoxysilane (18), 9-anthracenecarboxylic acid (2) and chloromethyltriethoxysilane are used as reactants. This reactant is mixed with triethylamine and methyl isobutyl ketone (MINK) previously dried over 4 cm molecular sieve to form a reaction mixture, which is heated to reflux and refluxed for about 6-10 hours. The After reflux, the reaction mixture is cooled overnight to give a large amount of solid precipitate. The remaining solution is rotary evaporated, filtered through a silica gel column, a second rotary evaporation, and 9-anthracenecarboxy-methyltriethoxysilane (18) is added to a dark amber oily liquid (this may be purified). ) Get as. This method includes 9-anthracenecarboxy-alkyltrialkoxysilanes (eg, including 9-anthracenecarboxy-ethyltriethoxysilane, 9-anthracenecarboxy-propyltrimethoxysilane, and 9-anthracenecarboxy-propyltriethoxysilane) This is important because it is suitable for use in making any compound of the group.

pH adjuster
A pH adjuster is a compound, material, or solution that is added to a mixture of a spin-on material and an absorbing organic compound that “adjusts” or adjusts the pH of the final spin-on composition to any resist selected. Also compatible or more compatible with materials (including those with absorption peaks around 365 nm, 248 nm, 193 nm, and 157 nm).

  However, this pH modifier not only adjusts the pH of the final spin-on composition, but also the chemical performance and properties of the final spin-on composition that is part of the layered material, electronic component, or semiconductor component It should also be noted that the spin-on composition is more compatible with the resist material being combined, affecting the mechanical performance and structural configuration. More specifically, the pH adjusting agent has a strong influence on the polymer characteristics, the structural configuration, and the spatial orientation, and improves the surface characteristics of the antireflection film so that optimum resist performance can be obtained. That is, a pH adjusting agent that does not affect the mechanical performance and structural configuration of the spin-on composition and the resist material to be combined simply by adjusting the pH of the spin-on material is not intended in this specification.

  Possible pH modifiers have two separate and sometimes related functions: a) affects the pH of the added composition; and b) the mechanical performance of the spin-on composition and / or Or affects the structural composition (which strongly affects polymer properties, structural composition, and spatial orientation, and improves the surface properties of the anti-reflective coating for optimal resist performance. Can also).

  Possible pH adjusters are designed in part to affect the pH of the composition to which the pH adjuster is added. Potential pH modifier compounds include: a) any suitable acidic or basic solution, compound, and / or ingredient, and / or b) any suitable strength and concentration of acidic or basic. Solutions, compounds, and / or ingredients are included. The appropriate pH “influencer” set is the largest set of compounds for which the final pH modifier is selected. This is because the pH “influencer” affects the mechanical performance and / or structural configuration of the final spin-on composition and can make the final spin-on composition adaptable or more adaptable. Because it must be. This means, for example, that the selected pH modifier is also designed to suit the solubility parameters, molecular weight, melting point, or some other physical property of the mixture of the spin-on material and the absorbing organic compound. Means. In other words, the pH adjusting agent and the mixture of the spin-on material and the absorbing organic compound are in accordance with preferable physical properties even when the pH adjusting agent exerts the first function of affecting the pH of the mixture. Must not be physically incompatible. In a preferred embodiment, the preferred physical property is a solubility parameter or molecular weight. In a further preferred embodiment, the preferred physical property is a solubility parameter.

  In addition, the adjusting agent may have a mechanical and structural influence on the function and properties of the combination of the resist material and the ARC. For example, a pH adjusted spin-on composition is applied to a substrate or layered material, and then a resist material is applied to the spin-on composition. When the resist material is exposed, it is then developed at an angle of 85-90 ° to the spin-on composition (development line). That is, the resist material does not “collapse” on the spin-on composition and has a useful development line. If the spin-on composition is not pH adjusted, the resist material may “collapse” into the spin-on composition after etching, which clearly results in problematic resist materials and / or problematic layered materials. In this example, the pH adjusted spin-on composition affects the mechanical and structural strength of the final spin-on composition and the compatibility of the resist material and ARC combination. As used herein, the term “combined” or “combination” means that two materials or compositions are placed on top of each other and the two materials are physical, mechanical and / or chemical. Means that they are bonded to each other.

  Some suitable pH adjusters include, for example, various molar concentrations of amines (eg, γ-aminoalkyltrialkoxysilanes, especially γ-aminopropyltriethoxysilanes (APTF or APTEOS)); water Oxides and alkoxides (eg, sodium alkoxide, potassium alkoxide, potassium hydroxide, etc.); hydrogen halides (eg, hydrogen bromide, hydrochloric acid); acetic acid; sulfuric acid, lactic acid, nitric acid; TMAH; propylene glycol methyl ether acetate (PGMEA) Amine-based oligomers (including oligomers containing inorganic atoms such as silicon), and combinations thereof. Possible pH modifier molar concentrations include pure (bulk), 10 molar, 1.0 molar, 0.1 molar, and 0.01 molar concentrations, depending on the pH agent chosen depending on the resist material. .

  Possible resist materials include all photolithography resist materials, including those having wavelength bands around 157 nm, 193 nm, 248 nm, and 365 nm. The reason for the wide range of resist materials is that any photolithographic resist material can be combined with the anti-reflective coating by the pH adjusting agent and they can be matched to each other. Among the possible photolithographic resist materials are acrylate-based resist materials, epoxy-based chemically amplified resists, fluoropolymer resists (these are particularly effective when considering an absorption wavelength of 157 nm) , Poly (norbornene-maleic anhydride) alternating copolymers, polystyrene-based, and diazonaphthoquinone / novolak resists.

Manufacturing Method From another aspect of the present invention, a method for synthesizing the absorptive spin-on composition described herein is provided. Spin-on materials typically include various silane reactants (eg, triethoxysilane (HTEOS), tetraethoxysilane (TEOS), methyltriethoxysilane (MTEOS), dimethyldiethoxysilane, tetramethoxysilane (TMOS). , Methyltrimethoxysilane (MTMOS), trimethoxysilane, dimethyldimethoxysilane, phenyltriethoxysilane (PTEOS), phenyltrimethoxysilane (PTMOS), diphenyldiethoxysilane, and diphenyldimethoxysilane) . However, gallium, arsenic, germanium, boron, and similar atoms and materials can also be used in conjunction with silicon atoms or as a single atomic material to produce spin-on materials.

  In addition, chlorosilanes (for example, trichlorosilane, methyltrichlorosilane, ethyltrichlorosilane, phenyltrichlorosilane, tetrachlorosilane, dichlorosilane, methyldichlorosilane, dimethyldichlorosilane, chlorotriethoxysilane, chlorotrimethoxysilane, chloromethyltriethoxy) Halosilanes including silane, chloroethyltriethoxysilane, chlorophenyltriethoxysilane, chloromethyltrimethoxysilane, chloroethyltrimethoxysilane, and chlorophenyltrimethoxysilane) can be used as the silane reactant.

  Generally, to produce an absorbing spin-on composition, an absorbing compound (eg, absorbing compounds 1-41) or a combination thereof is mixed with a silane reactant during the synthesis of the SOG material. A pH adjuster may be mixed with the silane reactant during or after the synthesis of the SOG material.

  One possible method for producing an absorbent spin-on composition is at least one inorganic-based composition, at least one absorbable organic compound, at least one pH adjuster, acid / water mixture. (E.g., nitric acid / water mixture), and mixing at least one solvent to form a reaction mixture; and refluxing the reaction mixture to produce an absorbing spin-on composition. The resulting spin-on composition is then diluted with at least one solvent to provide a coating solution that produces films of various thicknesses. Further, the pH adjusting agent can be added during or after the refluxing step.

  In addition to the absorbable spin-on composition, possible production methods include: at least one inorganic-based composition, at least one absorbable organic compound, at least one pH adjuster, and at least one solvent. Are mixed to produce a reaction mixture. The reaction mixture is then refluxed to produce an absorptive spin-on composition. The resulting spin-on composition is diluted with at least one solvent to provide a coating solution that produces films of various thicknesses. There are various conventionally used acid / water mixtures as pH adjusters in this method. Different acids may be added, less acid may be added, or more water may be added. Also good. However, whatever pH modifier is selected, not only the pH is affected by the pH modifier, but also the chemical, mechanical, and physical properties of ARC, and the combination of resist and ARC. The basic principle of better conformance is maintained.

  More specifically, silane reactants (eg, HTEOS, or TEOS and MTEOS, TMOS and MTMOS); or alternatively, tetrachlorosilane and methyltrichlorosilane, at least one absorbent compound (eg, absorbent compound) A reaction mixture is formed in the reaction vessel comprising at least one pH adjusting agent (eg APTF); solvent or combination of solvents; and an acid / water mixture. Suitable solvents include acetone, 2-propanol, and other simple alcohols, ketones, and esters (eg, 1-propanol, MIBK, propoxypropanol, and propyl acetate). The acid / water mixture is, for example, nitric acid and water. Other protic acids or acid anhydrides (eg acetic acid, formic acid, hydrochloric acid, or acetic anhydride) are used instead in the acid mixture. The resulting mixture is refluxed for about 1-24 hours to produce an absorbing spin-on solution. As mentioned above, the pH adjusting agent can be added during or after the refluxing step, depending on the resist material selected. Also, as noted above, the acid concentration and / or strength in the acid / water mixture, and the water concentration is selected from the resist material selected for the specific layered material, electronic component, or semiconductor component application. Depending on the pH, it may be varied to be a pH adjuster.

  The absorbing spin-on material can be diluted with a suitable solvent to obtain coating solutions that produce films of various thicknesses. Suitable diluent solvents include acetone, 2-propanol, ethanol, butanol, methanol, propyl acetate, ethyl lactate, propylene glycol propyl ether (referred to industrially as propanol-P). High boiling diluent solvents such as ethyl lactate and propylene glycol propyl ether have been found to be advantageous. High boiling solvents reduce the likelihood of film bubble defects. On the contrary, the low boiling point solvent may be trapped in the top layer (surface layer) of the crosslinked film and become voids (voids) when moved in the subsequent baking step. Additional solvents useful in the present invention include ethylene glycol dimethyl ether (also referred to as glyme), anisole, dibutyl ether, dipropyl ether, propylene glycol methyl ether acetate, pentanol. Additionally, surfactants (eg FC430, a product offered by 3M (Minneapolis, MN) or Megaface R08, a product offered by DIC (Japan)) should also be added to the coating solution. Can do. The coating solution is typically about 0.5-20% polymer by weight. Prior to use, the coating solution is filtered by standard filtration methods.

  According to a second method of producing an absorptive spin-on material, at least one silane reactant, at least one absorptive compound (e.g., absorptive compound 1-41), at least one pH adjuster, and a solvent or solvent A reaction mixture comprising a mixture of is formed in a reaction vessel. The reaction mixture is heated to reflux or refluxed for about 1-24 hours. The silane reactant and the solvent are those described in the first method. The above acid / water mixture is added to the reaction mixture with stirring. The resulting mixture is heated to reflux and reflux for about 1 to 24 hours to produce an absorptive and pH adjusted spin-on material. The absorbent spin-on material is diluted and filtered as described above to produce a coating solution. Also, as mentioned above, the pH adjuster may be added during the first reflux step or after the reflux step.

  A method of producing an absorbent organohydridosiloxane material produces a mixture of a two-phase solvent comprising a nonpolar solvent and a polar solvent and a phase transfer catalyst; adding at least one organotrihalosilane, hydridotrihalosilane; At least one pH adjusting agent is added; further, at least one absorbent compound (eg, absorbent compounds 1-41) is formed to form a two-phase reaction mixture; and further, the two-phase reaction mixture is allowed to react for about 1-24 hours Reacting to form an absorbable organohydridosiloxane polymer. Examples of the phase transfer catalyst include, but are not limited to, tetrabutylammonium chloride and benzyltrimethylammonium chloride. Nonpolar solvents include, but are not limited to, pentane, hexane, heptane, cyclohexane, benzene, toluene, xylene, halogenated solvents (eg, carbon tetrachloride), and mixtures thereof. . Useful polar solvents include water, alcohol, and mixtures of alcohol and water. The light absorbing polymer solution is diluted and filtered as described above to produce a coating solution.

A solution for spin-on coating, which is pH-adjusted by coating absorption, is applied to various substrates, and a layered material, a film used in the manufacture of semiconductors, or a film used in electronic components is a specific manufacturing method (typically Specifically, it is formed according to a conventional spin-on deposition method. These methods include a dispense spin, a thickness spin, and a thermal baking process to produce an absorptive SOG anti-reflective coating. A typical method includes a thickness spin of about 20 seconds at 1000 to 4000 rpm, and a bake step at a temperature of 2 or 3 80 ° C to 300 ° C for about 1 minute each. The absorptive and pH adjusted spin-on antireflective coating of the present invention has a refractive index of about 1.3 to about 2.0 and an extinction coefficient greater than about 0.07.

  Substrates contemplated herein include preferred substantially solid materials. Particularly preferred substrate layers include films, glass, ceramics, plastics, metals or coated metals, or composite materials. In a preferred embodiment, the substrate includes a silicon or germanium arsenic die or wafer surface, a packaging surface (e.g. found in copper, silver, nickel or gold plated lead frames), a copper surface (e.g. , Found in circuit boards), or package interconnect traces, via-walls or stiffener interfaces (“copper” is the term copper (bare copper) and copper Oxides), polymer based packages or substrate interfaces (eg found on polyimide based flex packages, lead or other metal alloy solder ball surfaces), glass and polymers (eg polymimide). In more preferred embodiments, the substrate includes materials common in the packaging and circuit board industries (eg, silicon, copper, glass, and other polymers).

  A general method for using the absorbing spin-on glass material of the present invention as an anti-reflective coating in a photolithography process is shown in FIGS. As shown in FIG. 2 a, a dielectric layer 22 is deposited on the silicon substrate 20. Dielectric layer 22 can be a variety of dielectric materials (eg, silicon dioxide layers derived from TEOS, silane-based silicon dioxide layers, thermally grown oxide, or methyl deposited by chemical vapor deposition). And other components and compounds into which hydridosiloxane or silicon dioxide is introduced). The dielectric layer 22 is typically an optically transparent medium, but may not be optically transparent. Absorbent and pH-adjusted spin-on antireflective coating layer 24 is applied over dielectric layer 22 (FIG. 2b) and covered with a photoresist layer 26, which is a normal positive photoresist, and the laminate shown in FIG. 2c. Is manufactured. The stack of FIG. 2c is exposed with ultraviolet light 32 through a mask 30, as shown in FIG. 2d. During exposure, the absorptive and pH adjusted spin-on ARC layer 24 absorbs UV light 32 transmitted through the photoresist. Since the dielectric layer 22 is generally and usually transparent in the UV wavelength region, in the absence of the absorptive spin-on ARC layer 24, the UV light 32 is reflected by the silicon layer 20 and has a critical dimension (eg, exposed) Reduce the critical dimension 27) of photoresist. In this example, a positive photoresist that directly transfers an image is assumed. However, it should be noted that some organic dielectrics are not optically transparent.

  The exposed laminate is developed to produce the laminate of FIG. 2e. Absorbent and pH adjusted spin-on ARC layer 24 is resistant to conventional photoresist developers (eg, 2.5% solution of tetramethylammonium hydroxide (TMAH)). On the other hand, ARC layers (which have some of the chemistry of photoresist materials) are more sensitive to photoresist developers. Furthermore, absorbable and pH adjusted spin-on ARCs are resistant to the photoresist removal process, and organic ARCs are not considered resistant. Thus, the absorbable and pH adjusted spin-on layer can facilitate reworking of the photoresist without the need to recoat the ARC layer.

  Next, the pattern is etched through the opening of the photoresist layer 26 in the spin-on ARC layer 24 adjusted by the absorptivity to produce the etched laminate of FIG. 2f. The absorptive spin-on ARC layer 24 is etched using etching with a fluorocarbon having high selectivity to the photoresist. The reaction of the absorptive spin-on layer to the fluorocarbon etch provides the additional advantage of an absorptive, pH-tuned spin-on layer on the organic ARC layer (this requires an oxygen plasma etch). Oxygen plasma etching may also reduce the critical dimension of the developed photoresist because oxygen plasma also etches organic-based photoresists. Fluorocarbon plasma consumes less photoresist than oxygen plasma. In a shorter UV wavelength region, the film thickness of the photoresist layer in the exposure process shown in FIG. For example, at 193 nm, the thickness of the photoresist layer is estimated to be about 300 nm. Therefore, when such short wavelengths are used, it is important to provide an ARC layer that is selectively etched with respect to the photoresist.

  Fluorocarbon etching is continued through the dielectric layer 22 to obtain the stack of FIG. 2g. Photoresist layer 26 is partially consumed in this continued etching process. Finally, the photoresist layer 26 is removed using an oxygen plasma or hydrogen scavenging chemistry or by wet chemistry, and the spin-on ARC layer 24 is buffered oxygen etch (eg, standard hydrofluoric acid / water mixture, non- Aqueous fluoride, partially aqueous fluoride, or fully aqueous fluoride) or aqueous or non-aqueous organic amines are used for removal. Preferably, the spin-on ARC layer can be removed by a solution that exhibits excellent selectivity for the underlying dielectric layer. That is, the general photolithography method shown in FIGS. 2a to 2h shows the process advantage of an absorptive spin-on material as an antireflection coating layer and a sacrificial antireflection coating layer.

  The method of synthesizing an absorptive spin-on material that includes a pH modifier to combine and improve the compatibility of the resist material is described in the following examples. The solutions and films prepared in the following examples are prepared to be compatible with several photoresist materials, including those that absorb around 157 nm, 193 nm, 248 nm, and 375 nm. The An example of a resist material at 193 nm is an acrylate resist material.

[Example 1]
Synthesis of absorbing spin-on materials containing 9-anthracenecarboxy-methyltriethoxysilane and pH modifier
In a 22 liter flask, 6331.20 grams of 2-propanol, 3166.66 grams of acetone, 2263.78 grams of TEOS, 1639.78 grams of MTEOS, 958.97 grams of 9-anthracenecarboxy-methyltriethoxysilane, 119.24 grams of 0.1 M nitric acid, And 1425.58 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, 932.80 grams of butanol and 20650.0 g of ethyl lactate were added. This solution was filtered for use in pH adjustment experiments. A pH adjuster, 0.1 M nitric acid, was added to two separate solutions of 650 g of spin-on material having an initial pH of about 1.5. Nitric acid was added in the following amounts to achieve the following pH: a) 2.794 g (pH = 0.7); b) 0.293 g (pH = 0.75). APTEOS was added to two separate solutions of 650 g of the same spin-on material in the following amounts: a) 0.053 g (pH = 4.13); b) '0.151 g (pH = 5. 47). Next, this solution was dispensed, rotated at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. The optical properties were measured by N & K Technology Model 1200 analyzer. The film thickness was 1402.17mm. At 248 nm, the refractive index (n) was 1.47 and the extinction coefficient (k) was 0.429. In all the following examples, the same spin process and firing process and measurement method were used.
Synthesis of other absorptive spin-on materials containing 9-anthracenecarboxy-methyltriethoxysilane and pH modifier
In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 60 grams 9-anthracenecarboxy-methyltriethoxysilane, 0.6 grams 0.1 M nitric acid, and 72 grams of deionized water was mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC430 (3M, Minneapolis, MN). . This solution was filtered. This solution was dispensed, and spind at 3000 rpm film thickness was performed for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer. The film thickness was 1635 mm. At 248 nm, the refractive index (n) was 1.373 and the extinction coefficient (k) was 0.268. However, it should be taken into account that the refractive index and extinction coefficient data in this example and the following planned examples will vary depending on the starting reactant and starting compound. In all the following examples, the same spin process, firing process and measurement method were used.
Synthesis of absorbing spin-on materials containing 9-anthracenecarboxy-methyltriethoxysilane and pH modifier
In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 60 grams 9-anthracenecarboxy-methyltriethoxysilane, 0.6 grams 0.01 M nitric acid, and 72 grams of deionized water was mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC430 (3M, Minneapolis, MN). . This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer. The film thickness was 1635 mm. At 248 nm, the refractive index (n) was 1.373 and the extinction coefficient (k) was 0.268.
Synthesis of absorbing spin-on materials containing 9-anthracenecarboxy-methyltriethoxysilane and pH modifier
In a 1-liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 60 grams 9-anthracenecarboxy-methyltriethoxysilane, 0.6 grams 1.0 M nitric acid, And 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC430 (3M, Minneapolis, MN). . This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer. The film thickness was 1635 mm.
Synthesis of absorbing spin-on materials containing 9-anthracenecarboxy-methyltriethoxysilane and pH modifier
In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 60 grams 9-anthracenecarboxy-methyltriethoxysilane, 0.6 grams 0.1 M nitric acid, and 100 grams of deionized water was mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer. The film thickness was 1635 mm.
Synthesis of absorbing spin-on materials containing 9-anthracenecarboxy-methyltriethoxysilane and pH modifier
In a 1-liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 60 grams 9-anthracenecarboxy-methyltriethoxysilane, 0.6 grams 0.1 M nitric acid, And 130 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer. The film thickness was 1635 mm.
Synthesis of absorptive spin-on materials containing 9-anthracenecarboxy-methyltriethoxysilane and pH modifier
In a 1-liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 60 grams 9-anthracenecarboxy-methyltriethoxysilane, 0.6 grams 0.1 M nitric acid, And 77 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. 1 g of APTEOS was added to this solution at reflux. After reflux, the solution was charged with 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN ) Was added. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer. The film thickness was 1635 mm. At 248 nm, the refractive index (n) was 1.373 and the extinction coefficient (k) was 0.268.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-methyltriethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 60 grams of 9-anthracenecarboxy-methyltriethoxysilane, 0.6 grams of 0.1 M nitric acid, and 77 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. 1 g of APTEOS was added to the solution after refluxing. Also after reflux, the solution was added to 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis , MN) was added. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer. The film thickness was 1635 mm.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-ethyltriethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 60 grams of 9-anthracenecarboxy-ethyltriethoxysilane, 0.6 grams of 10 M acetic acid, and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-ethyltriethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 60 grams of 9-anthracenecarboxy-ethyltriethoxysilane, 0.6 grams of 1.0 M acetic acid, and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-ethyltriethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 60 grams of 9-anthracenecarboxy-ethyltriethoxysilane, 0.6 grams of pure (bulk) acetic acid, and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-ethyltriethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 60 grams of 9-anthracenecarboxy-ethyltriethoxysilane, 0.6 grams of 10 M acetic acid, and 100 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-ethyltriethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 60 grams of 9-anthracenecarboxy-ethyltriethoxysilane, 0.6 grams of 1.0 M acetic acid, and 130 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-ethyltriethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 60 grams of 9-anthracenecarboxy-ethyltriethoxysilane, 0.6 grams of pure (bulk) acetic acid, and 72 grams of deionized water were mixed. 1.0 g of potassium hydroxide was added before refluxing. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-ethyltriethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 60 grams of 9-anthracenecarboxy-ethyltriethoxysilane, 0.6 grams of 10 M acetic acid, and 72 grams of deionized water were mixed. 1.0 g potassium hydroxide was added at reflux. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-ethyltriethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 60 grams of 9-anthracenecarboxy-ethyltriethoxysilane, 0.6 grams of 1.0 M acetic acid, and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. 1.0 g of potassium hydroxide was added before refluxing. This solution also contained 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) Was added. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-propyltriethoxysilane and pH adjuster In a 1 liter flask, 178 grams 2-propanol, 89 grams acetone, 52 grams TEOS, 59 grams MTEOS, 29 grams of 9-anthracenecarboxy-propyltriethoxysilane, 3.3 grams of pure (bulk) lactic acid, and 40 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 26 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer. The thickness was 1487.1 angstroms; k = 0.4315; n = 1.4986.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-propyltriethoxysilane and pH adjuster In a 1 liter flask, 178 grams 2-propanol, 89 grams acetone, 52 grams TEOS, 59 grams MTEOS, 29 grams of 9-anthracenecarboxy-propyltriethoxysilane, 3.3 grams of 10 M lactic acid, and 40 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 26 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-propyltriethoxysilane and pH adjuster In a 1 liter flask, 178 grams 2-propanol, 89 grams acetone, 52 grams TEOS, 59 grams MTEOS, 29 grams of 9-anthracenecarboxy-propyltriethoxysilane, 3.3 grams of pure (bulk) lactic acid, and 40 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 26 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-propyltriethoxysilane and pH adjuster In a 1 liter flask, 178 grams 2-propanol, 89 grams acetone, 52 grams TEOS, 59 grams MTEOS, 29 grams of 9-anthracenecarboxy-propyltriethoxysilane, 3.3 grams of 1.0 M lactic acid, and 70 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 26 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-propyltriethoxysilane and pH adjuster In a 1 liter flask, 178 grams 2-propanol, 89 grams acetone, 52 grams TEOS, 59 grams MTEOS, 29 grams of 9-anthracenecarboxy-propyltriethoxysilane, 3.3 grams of 10 M lactic acid, and 90 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 26 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-propyltriethoxysilane and pH adjuster In a 1 liter flask, 178 grams of 2 propanol, 89 grams of acetone, 52 grams of TEOS, 59 grams of MTEOS, 29 Grams of 9-anthracenecarboxy-propyltriethoxysilane, 3.3 grams of 10 M lactic acid, and 40 grams of deionized water were mixed. 1.5 g of TMAH was added to this solution before refluxing. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 26 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-propyltriethoxysilane and pH adjuster In a 1 liter flask, 178 grams 2-propanol, 89 grams acetone, 52 grams TEOS, 59 grams MTEOS, 29 grams of 9-anthracenecarboxy-propyltriethoxysilane, 3.3 grams of 10 M lactic acid, and 40 grams of deionized water were mixed. 1.5 g of TMAH was added to this solution at reflux. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 26 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-propyltriethoxysilane and pH adjuster In a 1 liter flask, 178 grams 2-propanol, 89 grams acetone, 52 grams TEOS, 59 grams MTEOS, 29 grams of 9-anthracenecarboxy-propyltriethoxysilane, 3.3 grams of 10 M lactic acid, and 40 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. 1.5 g of TMAH was added to the solution after reflux. Also after reflux, the solution was added to 26 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis , MN). This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-propyltriethoxysilane and pH adjuster In a 1 liter flask, 178 grams 2-propanol, 89 grams acetone, 52 grams TEOS, 59 grams MTEOS, 29 grams of 9-anthracenecarboxy-propyltriethoxysilane, 3.3 grams of 10 M lactic acid, and 40 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 26 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was. This solution was filtered. This solution was dispensed, and spinning was performed at 3000 rpm film thickness for 20 seconds, and baked at 80 ° C. and 180 ° C. for 1 minute, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer. The thickness was 1487.1 angstroms; k = 0.4315; n = 1.4986.

[Example 2]
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 25 grams of 9-anthracenemethanol, 10 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid 0.6 grams of 0.1 M nitric acid and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 111 grams butanol, 459 grams 2-propanol, 230 grams acetone, 309 grams ethanol, 50 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was. Thickness = 1436 angstrom, n = 1.479, k = 0.1255.
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 25 grams of 9-anthracenemethanol, 10 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid 0.6 grams of 0.01 M nitric acid and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 111 grams butanol, 459 grams 2-propanol, 230 grams acetone, 309 grams ethanol, 50 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 25 grams of 9-anthracenemethanol, 10 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid 0.6 grams of 1.0 M nitric acid, and 72 grams of deionized water. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 111 grams butanol, 459 grams 2-propanol, 230 grams acetone, 309 grams ethanol, 50 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 25 grams of 9-anthracenemethanol, 10 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid 0.6 grams of 0.1 M nitric acid and 95 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 111 grams butanol, 459 grams 2-propanol, 230 grams acetone, 309 grams ethanol, 50 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 25 grams of 9-anthracenemethanol, 10 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid 0.6 grams of 0.1 M nitric acid and 110 grams of deionized water. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 111 grams butanol, 459 grams 2-propanol, 230 grams acetone, 309 grams ethanol, 50 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 25 grams of 9-anthracenemethanol, 10 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid 0.6 grams of 0.1 M nitric acid and 72 grams of deionized water were mixed. 1.2 g of APTEOS was added to this solution before refluxing. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 111 grams butanol, 459 grams 2-propanol, 230 grams acetone, 309 grams ethanol, 50 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 25 grams of 9-anthracenemethanol, 10 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid 0.6 grams of 0.1 M nitric acid and 72 grams of deionized water were mixed. 1.2 g of APTEOS was added to this solution at reflux. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 111 grams butanol, 459 grams 2-propanol, 230 grams acetone, 309 grams ethanol, 50 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbing spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster In a 1 liter flask, 297 grams of 2-propanol , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 25 grams of 9-anthracenemethanol, 10 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid 0.6 grams of 0.1 M nitric acid and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. 1.2 g of APTEOS was added to the solution after reflux. Also after reflux, the solution was added to 111 grams butanol, 459 grams 2-propanol, 230 grams acetone, 309 grams ethanol, 50 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis , MN).

[Example 3]
Synthesis of absorbent SOG containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 93 grams of TEOS, 77 grams of MTEOS, 20 grams of 9-anthracenemethanol, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid, 0.5599 grams of 10 M acetic acid and 71.90 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent SOG containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 93 grams of TEOS, 77 grams of MTEOS, 20 grams of 9-anthracenemethanol, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid, 0.5599 grams of 1.0 M acetic acid and 71.90 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent SOG containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 93 grams of TEOS, 77 grams of MTEOS, 20 grams of 9-anthracenemethanol, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid, 0.5599 grams of pure (bulk) acetic acid and 71.90 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent SOG containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 93 grams of TEOS, 77 grams of MTEOS, 20 grams of 9-anthracenemethanol, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid, 0.5599 grams of 10 M acetic acid and 95 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent SOG containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 93 grams of TEOS, 77 grams of MTEOS, 20 grams of 9-anthracenemethanol, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid, 0.5599 grams of 10 M acetic acid and 120 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent SOG containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 93 grams of TEOS, 77 grams of MTEOS, 20 grams of 9-anthracenemethanol, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid, 0.5599 grams of 10 M acetic acid and 71.90 grams of deionized water were mixed. 2.2 g of potassium hydroxide was added to this solution before refluxing. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent SOG containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 93 grams of TEOS, 77 grams of MTEOS, 20 grams of 9-anthracenemethanol, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid, 0.5599 grams of 10 M acetic acid and 71.90 grams of deionized water were mixed. 2.2 g of potassium hydroxide was added to this solution at reflux. The flask was refluxed and / or heated for 1-12 hours. To this solution, 57 grams of butanol, 88 grams of 2-propanol, 44 grams of acetone, 59 grams of ethanol, 9.5 grams of deionized water, and 3.75 grams of 10% FC 430. (3M, Minneapolis, MN) added.
Synthesis of absorbent SOG containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 93 grams of TEOS, 77 grams of MTEOS, 20 grams of 9-anthracenemethanol, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid, 0.5599 grams of 1075
M acetic acid and 71.90 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. 2.2 g of potassium hydroxide was added to the solution after reflux. Also, after reflux, the solution was charged with 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis , MN).

[Example 4]
Synthesis of absorbent SOG containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 108 grams of TEOS, 77 grams of MTEOS, 10 grams of 9-anthracenemethanol, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid, 0.5599 grams of 0.1 M nitric acid and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was. Thickness = 4275mm, n = 1.529, k = 0.124.
Synthesis of absorbent SOG containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 108 grams of TEOS, 77 grams of MTEOS, 10 grams of 9-anthracenemethanol, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid, 0.5599 grams of 0.01 M nitric acid and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was. Thickness = 4275mm, n = 1.529, k = 0.124.
Synthesis of absorbent SOG containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 108 grams of TEOS, 77 grams of MTEOS, 10 grams of 9-anthracenemethanol, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid, 0.5599 grams of 1.0 M nitric acid and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was. Thickness = 4275mm, n = 1.529, k = 0.124.
Synthesis of absorbable SOG containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, rosoleic acid, and pH adjuster
In a 1-liter flask, 297 grams of 2-propanol, 148 grams of acetone, 108 grams of TEOS, 77 grams of MTEOS, 10 grams of 9-anthracenemethanol, 60 grams of 2-hydroxy-4- (3-tri Ethoxysilpropoxy) -diphenyl ketone, 5 grams of rosoleic acid, 0.5599 grams of 0.1 M nitric acid, and 95 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was. Thickness = 4275mm, n = 1.529, k = 0.124.
Synthesis of absorbent SOG containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 108 grams of TEOS, 77 grams of MTEOS, 10 grams of 9-anthracenemethanol, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid, 0.5599 grams of 0.1 M nitric acid and 125 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was. Thickness = 4275mm, n = 1.529, k = 0.124.
Synthesis of absorbent SOG containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 108 grams of TEOS, 77 grams of MTEOS, 10 grams of 9-anthracenemethanol, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid, 0.5599 grams of 0.1 M nitric acid and 72 grams of deionized water were mixed. 3 g of APTEOS was added to this solution before refluxing. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC430 (3M, Minneapolis, MN). . Thickness = 4275mm, n = 1.529, k = 0.124.
Synthesis of absorbent SOG containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosolic acid, and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 108 grams of TEOS, 77 grams of MTEOS, 10 grams of 9-anthracenemethanol, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid, 0.5599 grams of 0.1 M nitric acid and 72 grams of deionized water were mixed. 3 g of APTEOS was added to this solution at reflux. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was. Thickness = 4275mm, n = 1.529, k = 0.124.
Synthesis of absorbent SOG containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 108 grams of TEOS, 77 grams of MTEOS, 10 grams of 9-anthracenemethanol, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 5 grams of rosoleic acid, 0.5599 grams of 0.1 M nitric acid and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. 3 g of APTEOS was added to the solution after reflux. Also, after reflux, the solution was charged with 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis , MN). Thickness = 4275mm, n = 1.529, k = 0.124.

[Example 5]
Synthesis of absorbent spin-on material containing 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams Of TEOS, 51 grams of MTEOS, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 0.6 grams of 0.1 M nitric acid, and 72 grams of deionized water. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was. Thickness = 3592mm, n = 1.563, k = 0.067.
Synthesis of absorbent spin-on material containing 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams Of TEOS, 51 grams of MTEOS, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 0.6 grams of 0.01 M nitric acid, and 72 grams of deionized water. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams Of TEOS, 51 grams of MTEOS, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 0.6 grams of 1.0 M nitric acid, and 72 grams of deionized water. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 51 grams of MTEOS, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 0.6 grams of 0.1 M nitric acid, and 90 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams Of TEOS, 51 grams of MTEOS, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 0.6 grams of 0.1 M nitric acid, and 125 grams of deionized water. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams Of TEOS, 51 grams of MTEOS, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 0.6 grams of 0.1 M nitric acid, and 72 grams of deionized water. 0.26 g of APTEOS was added to this solution before refluxing. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams Of TEOS, 51 grams of MTEOS, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 0.6 grams of 0.1 M nitric acid, and 72 grams of deionized water. 0.26 g of APTEOS was added to this solution during the reflux step. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams Of TEOS, 51 grams of MTEOS, 60 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 0.6 grams of 0.1 M nitric acid, and 72 grams of deionized water. The flask was refluxed and / or heated for 1-12 hours. 0.26 g of APTEOS was added to the solution after reflux. After reflux, 57 grams of butanol, 88 grams of 2-propanol, 44 grams of acetone, 59 grams of ethanol, 9.5 grams of deionized water, and 3.75 grams of 10% FC430 (3M, Minneapolis, Minn.) Added to the solution.
Synthesis of absorbable spin-on material containing 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenyl ketone and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams Of TEOS, 51 grams of MTEOS, 60 grams of 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenyl ketone, 0.6 grams of 10 M lactic acid, and 72 grams of deionized water. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbable spin-on material containing 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenyl ketone and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams Of TEOS, 51 grams of MTEOS, 60 grams of 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenyl ketone, 0.6 grams of 1.0 M lactic acid, and 72 grams of deionized water. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbable spin-on material containing 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenyl ketone and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams Of TEOS, 51 grams of MTEOS, 60 grams of 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenyl ketone, 0.6 grams of 1.0 M lactic acid, and 72 grams of deionized water. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenylketone and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams Of TEOS, 51 grams of MTEOS, 75 grams of 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenyl ketone, 0.6 grams of 10 M lactic acid, and 72 grams of deionized water. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenylketone and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams Of TEOS, 51 grams of MTEOS, 60 grams of 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenyl ketone, 0.6 grams of 10 M lactic acid, and 115 grams of deionized water. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC430 (3M, Minneapolis, MN). .
Synthesis of absorbent spin-on material containing 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenylketone and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams Of TEOS, 51 grams of MTEOS, 60 grams of 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenyl ketone, 0.6 grams of 10 M lactic acid, and 72 grams of deionized water. 0.06 g of APTEOS was added to this solution before refluxing. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbable spin-on material containing 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenyl ketone and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams Of TEOS, 51 grams of MTEOS, 60 grams of 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenyl ketone, 0.6 grams of 10 M lactic acid, and 72 grams of deionized water. 0.06 g of APTEOS was added to this solution at reflux. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenylketone and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams Of TEOS, 51 grams of MTEOS, 60 grams of 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenyl ketone, 0.6 grams of 10 M lactic acid, and 72 grams of deionized water. The flask was refluxed and / or heated for 1-12 hours. 0.06 g of APTEOS was added to the solution after refluxing. After reflux, 57 grams of butanol, 88 grams of 2-propanol, 44 grams of acetone, 59 grams of ethanol, 9.5 grams of deionized water, and 3.75 grams of 10% FC 430 (3M, Minneapolis, Minn.) Added to.

[Example 6]
Synthesis of absorbing spin-on material containing 9-anthracene methanol and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 10 grams of 9- Anthracene methanol, 0.6 grams of 0.1 M hydrochloric acid, and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbing spin-on material containing 9-anthracene methanol and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 10 grams of 9- Anthracene methanol, 0.6 grams of 0.01 M hydrochloric acid, and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC430 (3M, Minneapolis, MN). .
Synthesis of absorbing spin-on material containing 9-anthracene methanol and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 10 grams of 9- Anthracene methanol, 0.6 grams of 1.0 M hydrochloric acid, and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbing spin-on material containing 9-anthracene methanol and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 10 grams of 9- Anthracene methanol, 0.6 grams 0.1 M hydrochloric acid, and 100 grams deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbing spin-on material containing 9-anthracene methanol and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 10 grams of 9- Anthracene methanol, 0.6 grams 0.1 M hydrochloric acid, and 130 grams deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbing spin-on material containing 9-anthracene methanol and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 10 grams of 9- Anthracene methanol, 0.6 grams of 0.1 M hydrochloric acid, and 72 grams of deionized water were mixed. 1.2 g of potassium hydroxide was added to this solution before refluxing. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbing spin-on material containing 9-anthracene methanol and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 10 grams of 9- Anthracene methanol, 0.6 grams of 0.1 M hydrochloric acid, and 72 grams of deionized water were mixed. 1.2 g of potassium hydroxide was added to this solution at reflux. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC430 (3M, Minneapolis, MN). .
Synthesis of absorbing spin-on material containing 9-anthracene methanol and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 10 grams of 9- Anthracene methanol, 0.6 grams of 0.1 M hydrochloric acid, and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. 1.2 g of potassium hydroxide was added to the solution after reflux. Also after reflux, 57 grams of butanol, 88 grams of 2-propanol, 44 grams of acetone, 59 grams of ethanol, 9.5 grams of deionized water, and 3.75 grams of 10% FC 430 (3M, Minneapolis, Minn.) Added to this solution.

[Example 7]
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 20 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 25 grams of 9-anthracenemethanol, and 5 grams of rosole Acid, 0.6 grams of 1.0 M acetic acid, and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was. Thickness = 3503mm, n = 1.475, k = 0.193.
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 20 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 25 grams of 9-anthracenemethanol, and 5 grams of rosole Acid, 0.6 grams of 10 M acetic acid, and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 20 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 25 grams of 9-anthracenemethanol, and 5 grams of rosole Acid, 0.6 grams of pure M (bulk) acetic acid, and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC430 (3M, Minneapolis, MN). .
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 20 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 25 grams of 9-anthracenemethanol, and 5 grams of rosole Acid, 0.6 grams of 10 M acetic acid, and 98 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 20 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 25 grams of 9-anthracenemethanol, and 5 grams of rosole Acid, 0.6 grams of 10 M acetic acid, and 120 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 20 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 25 grams of 9-anthracenemethanol, and 5 grams of rosole Acid, 0.6 grams of 10 M acetic acid, and 72 grams of deionized water were mixed. 1.5 g of TMAH was added to this solution before refluxing. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 20 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 25 grams of 9-anthracenemethanol, and 5 grams of rosole Acid, 0.6 grams of 10 M acetic acid, and 72 grams of deionized water were mixed. 1.5 g of TMAH was added to this solution at reflux. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 20 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 25 grams of 9-anthracenemethanol, and 5 grams of rosole Acid, 0.6 grams of 10 M acetic acid, and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. 1.5 g of TMAH was added to the solution after refluxing. Also after reflux, 57 grams of butanol, 88 grams of 2-propanol, 44 grams of acetone, 59 grams of ethanol, 9.5 grams of deionized water, and 3.75 grams of 10% FC 430 (3M, Minneapolis, Minn.) Added to this solution.

[Example 8]
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 5 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 25 grams of 9-anthracene methanol, and 5 grams of rosole Acid, 0.6 grams of 10 M lactic acid, and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was. Thickness = 3119mm, n = 1.454, k = 0.175.
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 5 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 25 grams of 9-anthracenemethanol, and 5 grams of rosole Acid, 0.6 grams of 1.0 M lactic acid, and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 5 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 25 grams of 9-anthracene methanol, and 5 grams of rosole Acid, 0.6 grams of pure (bulk) lactic acid, and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 5 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 25 grams of 9-anthracene methanol, and 5 grams of rosole Acid, 0.6 grams of 10 M lactic acid, and 100 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 5 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 25 grams of 9-anthracene methanol, and 5 grams of rosole Acid, 0.6 grams of 10 M lactic acid, and 130 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC430 (3M, Minneapolis, MN). .
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 5 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 25 grams of 9-anthracene methanol, and 5 grams of rosole Acid, 0.6 grams of 10 M lactic acid, and 72 grams of deionized water were mixed. 0.1 g of APTEOS was added to this solution before refluxing. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 5 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 25 grams of 9-anthracene methanol, and 5 grams of rosole Acid, 0.6 grams of 10 M lactic acid, and 72 grams of deionized water were mixed. 0.1 g of APTEOS was added to this solution at reflux. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN) It was.
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, and pH adjuster 297 grams of 2-propanol in a 1 liter flask , 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 5 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 25 grams of 9-anthracene methanol, and 5 grams of rosole Acid, 0.6 grams of 10 M lactic acid, and 72 grams of deionized water were mixed. The flask was refluxed and / or heated for 1-12 hours. 0.1 g of APTEOS was added to the solution after refluxing. Also after reflux, 57 grams of butanol, 88 grams of 2-propanol, 44 grams of acetone, 59 grams of ethanol, 9.5 grams of deionized water, and 3.75 grams of 10% FC 430 (3M, Minneapolis, Minn.) Added to this solution.

[Example 9]
Synthesis of absorbent spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, quinizarin, alizarin, and pH adjuster 297 grams in a 1 liter flask 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 20 grams 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 25 grams 9-anthracenemethanol, and 5 grams of rosoleic acid, 2 grams of quinizarin, 2 grams of alizarin, 0.6 grams of 0.1 M nitric acid, 1.0 M nitric acid, and 0.01 M nitric acid (added to three separate mixtures), and 72 grams Deionized water was mixed. In two other solutions containing 0.1 M nitric acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.7 grams 10% FC 430 (3M, Minneapolis, MN) It was. Thickness = 3554mm, n = 1.489, k = 0.193.

  In the other three solutions, 1.1 g potassium hydroxide was added. In each solution, potassium hydroxide was added before, during, and after the reflux step.

[Example 10]
Synthesis of absorbing spin-on material containing 9-anthracenemethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosoleic acid, alizarin, and pH adjuster 297 grams of 2 in a 1 liter flask -Propanol, 148 grams of acetone, 123 grams of TEOS, 51.5 grams of MTEOS, 5 grams of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenyl ketone, 25 grams of 9-anthracene methanol, 5 grams Rozolic acid and 2 grams of alizarin, 0.5599 grams of 1.0 M, 10 M, and pure (bulk) acetic acid (added to each of the three separate mixtures) and 71.90 grams of deionized water were mixed. In two other solutions containing 10 M acetic acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution is added 56.68 grams butanol, 87.99 grams 2-propanol, 44.10 grams acetone, 59.31 grams ethanol, 9.55 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, MN). It was.

  To the other three solutions, 0.25 g of APTEOS was added. In each solution, APTEOS was added before, during, and after the reflux step, respectively.

[Example 11]
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-methyltriethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 30 grams of 9-anthracenecarboxy-methyltriethoxysilane, 0.6 grams of 0.1 M, 0.01 M, and 1.0 M nitric acid (added to each of three separate solutions) and 72 grams of deionized water were mixed. . To the other two solutions containing 0.1 M nitric acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.7 grams 10% FC430 (3M, Minneapolis, MN). .

In the other three solutions, 0.25 g HCl was added. To each solution, HCl was added before, during, and after the reflux step, respectively.
Synthesis of absorbing spin-on material containing 9-anthracenecarboxy-ethyltriethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 30 grams of 9-anthracenecarboxy-ethyltriethoxysilane, 0.6 grams of 1.0 M, 10 M, and pure (bulk) lactic acid (each added to three separate solutions), and 72 grams of deionized water Mixed. To the other two solutions containing 10 M lactic acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.7 grams 10% FC 430 (3M, Minneapolis, MN) It was.

To the other three solutions, 1.2 g of APTEOS was added. APTEOS was added to each solution before, during, and after the reflux step, respectively.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-propyltriethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 30 grams of 9-anthracenecarboxy-propyltriethoxysilane, 0.6 grams of 1.0 M, 10 M, and pure (bulk) lactic acid (added to each of three separate solutions), and 72 grams of deionized water Mixed. In two other solutions containing 10M lactic acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.7 grams 10% FC 430 (3M, Minneapolis, MN) It was.

In the other three solutions, 0.2 g of APTEOS was added. APTEOS was added to each solution before, during, and after the reflux step, respectively.
Synthesis of absorbing spin-on material containing 9-anthracenecarboxy-pentyltriethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 30 grams of 9-anthracenecarboxy-pentyltriethoxysilane, 0.6 grams of 0.1 M, 0.01 M, and 1.0 M nitric acid (each added to three separate solutions) and 72 grams of deionized water were mixed. . In two other solutions containing 0.1 M nitric acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.7 grams 10% FC 430 (3M, Minneapolis, MN) It was.

In the other three solutions, 1.0 g of potassium hydroxide was added. To each solution, potassium hydroxide was added before, during, and after the reflux step, respectively.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-methyltrimethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 30 grams of 9-anthracenecarboxy-methyltrimethoxysilane, 0.6 grams of 1.0 M, 10 M, and pure (bulk) acetic acid (each added to three separate solutions), and 72 grams of deionized water Mixed. In two other solutions containing 10M acetic acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.7 grams 10% FC 430 (3M, Minneapolis, MN) It was.

In the other three solutions, 2.4 g of TMAH was added. To each solution, TMAH was added before, during, and after the reflux step, respectively.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-ethyltrimethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 30 grams of 9-anthracenecarboxy-ethyltrimethoxysilane, 0.6 grams of 1.0 M, 10 M, and pure (bulk) lactic acid (added to each of three separate solutions), and 72 grams of deionized water Mixed. In two other solutions containing 10M lactic acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.7 grams 10% FC 430 (3M, Minneapolis, MN) It was.

In the other three solutions, 1.2 g of APTEOS was added. APTEOS was added to each solution before, during, and after the reflux step, respectively.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-propyltrimethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 123 grams TEOS, 77 grams MTEOS, 30 grams of 9-anthracenecarboxy-propyltrimethoxysilane, 0.6 grams of 0.1 M, 0.01 M, and 1.0 M hydrochloric acid (added to each of three separate solutions) and 72 grams of deionized water were mixed. In two other solutions containing 0.1M hydrochloric acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.7 grams 10% FC 430 (3M, Minneapolis, MN) It was.

  In the other three solutions, 1.4 g of APTEOS was added. APTEOS was added to each solution before, during, and after the reflux step, respectively. .

[Example 12]
Synthesis of absorbent spin-on material containing 9-anthracenemethanol and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS and 10 grams of 9 -Anthracene methanol was mixed. The solution was refluxed for 6 hours. A mixture of 0.6 grams of 0.1 M, 0.01 M, and 1.0 M hydrochloric acid (each added to three separate solutions) and 72 grams of deionized water was mixed. In two other solutions containing 0.1M hydrochloric acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.7 grams 10% FC430 (3M, Minneapolis, MN). .

In the other three solutions, 1.4 g of APTEOS was added. APTEOS was added to each solution before, during, and after the reflux step, respectively.
9-Anthracene Synthesis of absorbent spin-on material containing ethanol and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS and 10 grams of 9 -Anthracene Ethanol was mixed. The solution was refluxed for 6 hours. A mixture of 0.6 grams of 0.1 M, 0.01 M, and 1.0 M nitric acid (each added to three separate solutions) and 72 grams of deionized water was mixed. In two other solutions containing 0.1 M nitric acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.7 grams 10% FC 430 (3M, Minneapolis, MN) It was.

In the other three solutions, 0.4 g of APTEOS was added. APTEOS was added to each solution before, during, and after the reflux step, respectively.
9-Anthracene Synthesis of absorbent spin-on material containing propanol and pH adjuster In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS and 10 grams of 9 -Anthracene Propanol was mixed. The solution was refluxed for 6 hours. A mixture of 0.6 grams of 1.0 M, 10 M, and pure (bulk) acetic acid (each added to three separate solutions) and 72 grams of deionized water was mixed. In two other solutions containing 10M acetic acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.7 grams 10% FC 430 (3M, Minneapolis, MN) It was.

  In the other three solutions, 1.25 g of TMAH was added. To each solution, TMAH was added before, during, and after the reflux step, respectively.

[Example 13]
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-methyltriethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 90 grams TMOS, 59 grams MTMOS, 60 grams of 9-anthracenecarboxy-methyltriethoxysilane, 0.6 grams of 1.0 M, 10 M, and pure (bulk) acetic acid (each added to three separate solutions), and 72 grams of deionized water Mixed. In two other solutions containing 10M acetic acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) did.

In the other three solutions, 1.25 g of TMAH was added. To each solution, TMAH was added before, during, and after the reflux step, respectively.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-ethyltriethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 90 grams TMOS, 59 grams MTMOS, 60 grams of 9-anthracenecarboxy-ethyltriethoxysilane, 0.6 grams of 0.1 M, 0.01 M, and 1.0 M nitric acid (added to each of three separate solutions) and 72 grams of deionized water were mixed. . In two other solutions containing 0.1 M nitric acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC430 (3M, Minneapolis, MN). .

In the other three solutions, 0.25 g of TMAH was added. To each solution, TMAH was added before, during, and after the reflux step, respectively.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-methyltrimethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 90 grams TMOS, 59 grams MTMOS, 60 grams of 9-anthracenecarboxy-methyltrimethoxysilane, 0.6 grams of 1.0 M, 10 M, and pure (bulk) lactic acid (added to each of three separate solutions), and 72 grams of deionized water Mixed. In two other solutions containing 10M lactic acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was.

In the other three solutions, 1.5 g of potassium hydroxide was added. To each solution, potassium hydroxide was added before, during, and after the reflux step, respectively.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-propyltriethoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 90 grams TMOS, 59 grams MTMOS, 60 grams of 9-anthracenecarboxy-propyltriethoxysilane, 0.6 grams of 0.1 M, 0.01 M, and 1.0 M nitric acid (added to each of three separate solutions) and 72 grams of deionized water were mixed. . In two other solutions containing 0.1 M nitric acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was.

In the other three solutions, 0.5 g of TMAH was added. To each solution, TMAH was added before, during, and after the reflux step, respectively.
Synthesis of absorbent spin-on material containing 9-anthracenecarboxy-methyltripropoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 90 grams TMOS, 59 grams MTMOS, 60 grams of 9-anthracenecarboxy-methyltripropoxysilane, 0.6 grams of 1.0 M, 10 M, and pure (bulk) acetic acid (each added to three separate solutions), and 72 grams of deionized water Mixed. In two other solutions containing 10M acetic acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was.

In the other three solutions, 0.75 g of TMAH was added. To each solution, TMAH was added before, during, and after the reflux step, respectively.
Synthesis of absorbing spin-on material containing 9-anthracenecarboxy-ethyltributoxysilane and pH adjuster In a 1 liter flask, 297 grams 2-propanol, 148 grams acetone, 90 grams TMOS, 59 grams MTMOS, 60 grams of 9-anthracenecarboxy-ethyltributoxysilane, 0.6 grams of 1.0 M, 10 M, and pure (bulk) acetic acid (each added to three separate solutions), and 72 grams of deionized water Mixed. In two other solutions containing 10M acetic acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution, add 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, and 3.8 grams 10% FC 430 (3M, Minneapolis, MN) It was.

In the other three solutions, 1.00 g of TMAH was added. To each solution, TMAH was added before, during, and after the reflux step, respectively.
[Example 14]
Synthesis of absorbing spin-on material containing phenyltriethoxysilane and pH adjuster In a 1 liter flask, 297 grams (4.798 mole) 2-propanol, 148 grams (2.558 mole) acetone, 123 grams (0.593 mole) TEOS, 104 grams (0.432 moles) of phenyltriethoxysilane, 0.6 grams of 1.0 M, 10 M, and pure (bulk) acetic acid (added to three separate solutions each), and 72 grams of deionized water Were mixed. In two other solutions containing 10M acetic acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 57 grams (0.769 mole) butanol, 88 grams (1.422 mole) 2-propanol, 44 grams (0.758 mole) acetone, 59 grams (1.227 mole) ethanol, 9.5 grams (0.528 mole). Ionized water was added. Thickness = 1727mm, n = 1.957, k = 0.384.

In the other three solutions, 1.00 g of TMAH was added. To each solution, TMAH was added before, during, and after the reflux step, respectively.
Synthesis of absorbing spin-on material containing phenyltrimethoxysilane and pH adjuster In a 1 liter flask, 297 grams (4.798 mole) 2-propanol, 148 grams (2.558 mole) acetone, 123 grams (0.593 mole) Mix TEOS, 104 grams (0.432 mole) phenyltriethoxysilane, 0.6 grams 0.1 M, 0.01 M, and 1.0 M nitric acid (each added to three separate solutions), and 72 grams deionized water did. In two other solutions containing 0.1 M nitric acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 57 grams (0.769 mole) butanol, 88 grams (1.422 mole) 2-propanol, 44 grams (0.758 mole) acetone, 59 grams (1.227 mole) ethanol, 9.5 grams (0.528 mole). Ionized water was added.

In the other three solutions, 1.00 g of APTEOS was added. APTEOS was added to each solution before, during, and after the reflux step, respectively.
Synthesis of absorbing spin-on material containing phenyltripropoxysilane and pH adjuster In a 1 liter flask, 297 grams (4.798 mole) 2-propanol, 148 grams (2.558 mole) acetone, 123 grams (0.593 mole) TEOS, 104 grams (0.432 moles) of phenyltriethoxysilane, 0.6 grams of 1.0 M, 10 M, and pure (bulk) lactic acid (added to three separate solutions each), and 72 grams of deionized water Were mixed. In two other solutions containing 10M lactic acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 57 grams (0.769 mole) butanol, 88 grams (1.422 mole) 2-propanol, 44 grams (0.758 mole) acetone, 59 grams (1.227 mole) ethanol, 9.5 grams (0.528 mole). Ionized water was added.

In the other three solutions, 0.75 g of APTEOS was added. APTEOS was added to each solution before, during, and after the reflux step, respectively.
Synthesis of absorbing spin-on material containing phenyltributoxysilane and pH adjuster In a 1 liter flask, 297 grams (4.798 mole) 2-propanol, 148 grams (2.558 mole) acetone, 123 grams (0.593 mole) TEOS, 104 grams (0.432 moles) of phenyltriethoxysilane, 0.6 grams of 1.0 M, 10 M, and pure (bulk) acetic acid (added to three separate solutions each), and 72 grams of deionized water Were mixed. In two other solutions containing 10M acetic acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 57 grams (0.769 mole) butanol, 88 grams (1.422 mole) 2-propanol, 44 grams (0.758 mole) acetone, 59 grams (1.227 mole) ethanol, 9.5 grams (0.528 mole). Ionized water was added.

In the other three solutions, 0.50 g of APTEOS was added. APTEOS was added to each solution before, during, and after the reflux step, respectively.
[Example 15]
Synthesis of Absorbing Spin-On Material Containing 4-Ethoxyphenylazobenzene-4-carboxy-methyltriethoxysilane and pH Adjuster In a 1 liter flask, 297 grams (4.798 moles) 2-propanol, 148 grams (2.558 moles) Acetone, 123 grams (0.593 mole) TEOS, 77 grams (0.432 mole) MTEOS, 44.5 grams (0.13 mole) 4-ethoxyphenylazobenzene-4-carboxy-methyltriethoxysilane, 0.6 grams 1.0 M, 10 M , And pure (bulk) acetic acid (each added to three separate solutions) and 72 grams of deionized water. In two other solutions containing 10M acetic acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 57 grams (0.769 mole) butanol, 88 grams (1.422 mole) 2-propanol, 44 grams (0.758 mole) acetone, 59 grams (1.227 mole) ethanol, 9.5 grams (0.528 mole). Ionized water was added.

In the other three solutions, 0.50 g of APTEOS was added. APTEOS was added to each solution before, during, and after the reflux step, respectively.
Synthesis of absorbing spin-on material containing 4-ethoxyphenylazobenzene-4-carboxy-ethyltriethoxysilane In a 1 liter flask, 297 grams (4.798 mole) 2-propanol, 148 grams (2.558 mole) acetone, 123 grams (0.593 mole) TEOS, 77 grams (0.432 mole) MTEOS, 44.5 grams (0.13 mole) 4-ethoxyphenylazobenzene-4-carboxy-methyltriethoxysilane, 0.6 grams 1.0 M, 10 M, and pure ( Bulk) lactic acid (each added to three separate solutions) and 72 grams of deionized water were mixed. In two other solutions containing 10M lactic acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 57 grams (0.769 mole) butanol, 88 grams (1.422 mole) 2-propanol, 44 grams (0.758 mole) acetone, 59 grams (1.227 mole) ethanol, 9.5 grams (0.528 mole). Ionized water was added.

In the other three solutions, 0.25 g of APTEOS was added. APTEOS was added to each solution before, during, and after the reflux step, respectively.
Synthesis of an absorbing spin-on material comprising 4-methoxyphenylazobenzene-4-carboxy- propyltriethoxysilane In a 1 liter flask, 297 grams (4.798 mole) 2-propanol, 148 grams (2.558 mole) acetone, 123 Grams (0.593 mole) TEOS, 77 grams (0.432 mole) MTEOS, 44.5 grams (0.13 mole) 4-ethoxyphenylazobenzene-4-carboxy-methyltriethoxysilane, 0.6 grams 0.1 M, 0.01 M, and 1.0 M nitric acid (each added to three separate solutions) and 72 grams of deionized water were mixed. In two other solutions containing 0.1 M nitric acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 57 grams (0.769 mole) butanol, 88 grams (1.422 mole) 2-propanol, 44 grams (0.758 mole) acetone, 59 grams (1.227 mole) ethanol, 9.5 grams (0.528 mole). Ionized water was added.

In the other three solutions, 0.10 g of APTEOS was added. APTEOS was added to each solution before, during, and after the reflux step, respectively.
Synthesis of absorbing spin-on material comprising 4-methoxyphenylazobenzene-4-carboxy- propyltrimethoxysilane In a 1 liter flask, 297 grams (4.798 moles) 2-propanol, 148 grams (2.558 moles) acetone, 123 Grams (0.593 mole) TEOS, 77 grams (0.432 mole) MTEOS, 44.5 grams (0.13 mole) 4-ethoxyphenylazobenzene-4-carboxy-methyltriethoxysilane, 0.6 grams 0.1 M, 0.01 M, and 1.0 M hydrochloric acid (each added to three separate solutions) and 72 grams of deionized water were mixed. In two other solutions containing 0.1 M hydrochloric acid, 90 g and 110 g of deionized water were added, respectively. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 57 grams (0.769 mole) butanol, 88 grams (1.422 mole) 2-propanol, 44 grams (0.758 mole) acetone, 59 grams (1.227 mole) ethanol, 9.5 grams (0.528 mole). Ionized water was added. n = 1.499, k = 0.162 (at 365 nm).

In the other three solutions, 0.50 g of TMAH was added. To each solution, TMAH was added before, during, and after the reflux step, respectively.
[Example 16]
Synthesis of absorbing spin-on material containing PGMEA and pH adjuster In a 1 liter flask, 504.829 g PGMEA, 123.6 grams TEOS, 76.9 grams MTEOS, 5.608 grams 0.1 M nitric acid, and 66.869 grams deionized Water was mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 43.777 grams of butanol. This solution was filtered for use in pH adjustment experiments.

  In another 1 liter flask, 297 grams of 2-propanol, 148.560 grams of acetone, 139.902 grams of TEOS, 19.10 grams of MTEOS, 51.7 grams of PTEOS, 5.624 grams of 0.1 M nitric acid, and 66.827 grams of deionized water. Mixed. The flask was refluxed and / or heated for 1-12 hours. To this solution was added 43.93 grams of butanol. This solution was filtered for use in pH adjustment experiments.

The two prepared solutions were mixed and the pH adjuster, APTEOS, was added to six separate solutions of 650 g of mixed spin-on material having an starting pH of about 1.7. APTEOS was added to the following pH: a) 1.49 g (pH = 807); b) 0.26 g (pH = 7.12); c) 0.1 g (pH = 6.29); d) 0.06 (pH = 5.50); e) 0.03 g (pH = 2.49); f) 0 grams (pH = 1.76). Next, this solution was dispensed, and spinning was performed at a film thickness of 3000 rpm for 20 seconds, followed by baking at 80 ° C. and 180 ° C. for 1 minute. Optical properties were measured with an N & K Technology Model 1200 analyzer. The optical properties of the above AF solution were as follows:
a) Thickness = 1686 Angstrom; k = 0.297; n = 1.802; Etch ratio (er) = 9.33
b) Thickness = 1332 Angstrom; k = 0.295; n = 1.802; etch ratio (er) = 8.5
c) Thickness = 1298 Angstroms; k = 0.294; n = 1.802; Etch ratio (er) = 8.316
d) Thickness = 1292 Å; k = 0.293; n = 1.802; etch ratio (er) = 8.17
e) Thickness = 1304.9 Angstrom; k = 0.292; n = 1.802; etch ratio (er) = 8.01
f) Thickness = 1263.9 Angstrom; k = 0.289; n = 1.802; etch ratio (er) = 7.83
Thus, specific embodiments, applications, and methods of compositions for producing spin-on materials, inorganic spin-on materials, and spin-on glass materials that contain an absorptive compound and further a pH adjuster are disclosed. It was. However, it will be apparent to those skilled in the art that many more modifications besides those already described are possible without departing from the inventive concepts herein. Accordingly, the subject matter of the present invention is not limited only to the appended claims. Further, in interpreting the specification and the claims, all terms should be interpreted in the broadest sense consistent with the context. In particular, the terms “comprising” and “consisting of” should be construed as indicating the element, component, or process non-exclusive, and the indicated element, component, or process. Indicates that it exists, can be used and combined with other elements, components or processes.

FIG. 1a shows the chemical formula of an absorptive compound that can be introduced into a spin-on glass composition. FIG. 1b shows the chemical formula of the absorbing compound that can be introduced into the spin-on glass composition. FIG. 1c shows the chemical formula of the absorbing compound that can be introduced into the spin-on glass composition. FIG. 1d shows the chemical formula of the absorbing compound that can be introduced into the spin-on glass composition. FIG. 1e shows the chemical formula of the absorbing compound that can be introduced into the spin-on glass composition. FIG. 1f shows the chemical formula of the absorbing compound that can be introduced into the spin-on glass composition. Figures 2a-h illustrate the use of an absorptive spin-on composition containing a modifier as an antireflective coating layer in a photolithography process.

Claims (42)

  An absorptive spin-on glass composition comprising at least one inorganic-based compound, at least one absorbable organic compound that can be introduced, and at least one pH adjusting agent.   The composition of claim 1, wherein the absorbing compound strongly absorbs light over a wavelength range of at least about 5 nm in width at wavelengths less than 375 nm.   The composition of claim 1, wherein the absorbing compound strongly absorbs light over a wavelength range of at least about 10 nm in width at wavelengths less than 375 nm.   The composition of claim 2, wherein the wavelength range is less than about 260 nm.   The absorptive compound comprises at least one benzene ring and a reactive group selected from the group comprising a hydroxyl group, an amine group, a carboxylic acid group, and a substituted silyl group. Composition.   The composition according to claim 5, wherein the absorbent compound comprises two or more benzene rings.   The composition according to claim 6, wherein the two or more benzene rings are condensed.   The absorptive organic compound is anthraflavic acid, 9-anthracenecarboxylic acid, 9-anthracenemethanol, alizarin, quinizarin, primuline, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosole Acid, triethoxysilylpropyl-1,8-naphthalimide, 9-anthracenecarboxy-alkyltriethoxysilane, phenyltriethoxysilane, 10-phenanthrenecarboxy-methyltriethoxysilane, 4-phenylazophenol, 4-ethoxyphenylazobenzene- 6. The composition of claim 5, comprising an absorbent compound comprising 4-carboxy-methyltriethoxysilane, 4-methoxyphenylazobenzene-4-carboxy-methyltriethoxysilane, and mixtures thereof.   The composition of claim 1, wherein the inorganic-based compound comprises a silicon-based compound.   The composition of claim 9, wherein the silicon-based compound comprises a polymer.   The said polymer comprises methylsiloxane, methylsilsesquioxane, phenylsiloxane, phenylsilsesquioxane, methylphenylsiloxane, methylphenylsilsesquioxane, silicate polymer, silazane polymer, and mixtures thereof. 11. The composition according to 10.   The polymer is hydrogen siloxane, hydrogen silsesquioxane, organic hydrido siloxane, and organic hydrido silsesquioxane polymer, copolymer of hydrogen silsesquioxane and alkoxy hydrido siloxane or hydroxy hydrido siloxane, and mixtures thereof The composition of claim 10 comprising: The polymer is (H _0-1.0 SiO _1.5-2.0 ) _x (where x is greater than about 4) and (H _0-1.0 SiO _1.5-2.0 ) _n (R _0-1.0 SiO _1.5-2.0 ) _{m wherein} m is greater than 0, the sum of n and m is from about 4 to about 5000, and R is a C ₁ -C ₂₀ alkyl. is a formula comprising a a) aryl groups or C ₆ -C _12, the composition of claim 10.   The composition of claim 1, wherein the pH adjuster comprises water.   The composition of claim 1, wherein the pH adjuster comprises a base.   The composition of claim 15, wherein the base comprises an amine.   The composition of claim 16, wherein the amine comprises an amine-based oligomer.   The composition of claim 1, wherein the pH adjuster comprises an acid.   A coating solution comprising the spin-on composition according to claim 1 and a solvent or a solvent mixture.   20. The coating solution of claim 19, wherein the solution is about 0.5 wt% to about 20 wt% spin-on composition. Mixing at least one silane reactant, at least one absorbable organic compound that can be introduced, at least one pH adjusting agent, an acid / water mixture, and one or more solvents to form a reaction mixture;
Heating the reaction mixture to produce a spin-on composition;
A process for producing a spin-on composition. Mixing at least one silane reactant, at least one absorbable organic compound that can be introduced, at least one pH adjuster, and one or more solvents to form a reaction mixture, wherein the pH adjuster Comprises at least one acid and water;
Heating the reaction mixture to produce a spin-on composition;
A process for producing a spin-on composition.   A substitution wherein the at least one absorptive organic compound is bonded with silicon to at least one benzene ring, at least one substituent comprising a hydroxyl group, an amine group, a carboxylic acid group, and an alkoxy group and a halogen atom. The method according to claim 21 or 22, comprising a reactive group comprising a silyl group.   The at least one absorbing organic compound is anthraflavic acid, 9-anthracenecarboxylic acid, 9-anthracenemethanol, alizarin, quinizarin, primulin, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, rosole Acid, triethoxysilylpropyl-1,8-naphthalimide, 9-anthracenecarboxy-alkyltriethoxysilane, phenyltriethoxysilane, 10-phenanthrenecarboxy-methyltriethoxysilane, 4-phenylazophenol, 4-ethoxyphenylazobenzene- An absorptive compound selected from the group consisting of 4-carboxy-methyltriethoxysilane, 4-methoxyphenylazobenzene-4-carboxy-methyltriethoxysilane, and mixtures thereof. The method according to claim 21 or 22.   The at least one silane reactant is triethoxysilane, tetraethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane, tetramethoxysilane, methyltrimethoxysilane, trimethoxysilane, dimethyldimethoxysilane, phenyltriethoxysilane, phenyl Trimethoxysilane, diphenyldiethoxysilane, and diphenyldimethoxysilane, trichlorosilane, methyltrichlorosilane, ethyltrichlorosilane, phenyltrichlorosilane, tetrachlorosilane, chlorotriethoxysilane, chlorotrimethoxysilane, chloromethyltriethoxysilane, chloroethyl Triethoxysilane, chlorophenyltriethoxysilane, chloromethyltrimethoxysilane, chloroethyltrimethoxysilane And comprising a chlorophenyl trimethoxysilane method according to claim 21 or 22.   The method of claim 21, wherein the pH adjuster comprises water.   The method of claim 21, wherein the pH adjuster comprises a base.   28. The method of claim 27, wherein the pH adjuster comprises an amine.   The method of claim 21, wherein the pH adjusting agent comprises an acid.   The method of claim 21, wherein the acid / water mixture comprises nitric acid, lactic acid, or acetic acid. At least one alkoxysilane or halosilane; at least one absorbable organic compound; at least one pH adjuster; an acid / water mixture; and one or more solvents are mixed to form a reaction mixture; further,
Heating the reaction mixture to form a spin-on polymer;
A method for producing a coating solution containing a spin-on material. At least one alkoxysilane or halosilane; at least one absorbable organic compound; at least one pH adjuster; and one or more solvents are mixed to form a reaction mixture, wherein the pH adjustment The agent comprises at least one acid and water;
Heating the reaction mixture to form a spin-on polymer;
A method for producing a coating solution containing a spin-on material. Adding one or more diluent solvents to the spin-on composition to prepare a coating solution;
The method according to claim 31 or 32, further comprising:   A layered material comprising the spin-on composition of claim 1 in combination with a resist material.   A layered material comprising the coating solution of claim 19 in combination with a resist material.   35. The layered material of claim 34, wherein the resist material comprises a development line at an angle of at least 85 [deg.] With respect to the spin-on composition.   36. The layered material of claim 35, wherein the resist material comprises a development line at an angle of at least 85 [deg.] With respect to the coating solution.   A semiconductor comprising the spin-on composition of claim 1.   20. A semiconductor comprising the coating solution of claim 19.   The composition of claim 1, wherein the composition is designed to be at least partially removed.   The composition of claim 1, wherein the pH adjusting agent comprises a compound selected to improve the compatibility of the resist material with the spin-on composition. 42. The composition of claim 41, wherein the resist material absorbs light over a wavelength range comprising 157 nm, 193 nm, 248 nm, and 365 nm.

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